methyl 2-[(2S,4S,6R)-6-(1,3-dithian-2-ylmethyl)-4-hydroxyoxan-2-yl]acetate | 325786-84-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二噻烷
• 英文名称: methyl 2-[(2S,4S,6R)-6-(1,3-dithian-2-ylmethyl)-4-hydroxyoxan-2-yl]acetate
• CAS: 325786-84-3
• 化学式: C₁₃H₂₂O₄S₂
• 分子量: 306.447
• InChiKey: QWNLIHQBVXLZKR-GARJFASQSA-N

物化性质

• 沸点：
  464.1±35.0 °C(predicted)
• 密度：
  1.220±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-[(2S,4S,6R)-6-(1,3-dithian-2-ylmethyl)-4-hydroxyoxan-2-yl]acetate 、 对硝基苯甲酸 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以85%的产率得到[(2R,4R,6S)-2-(1,3-dithian-2-ylmethyl)-6-(2-methoxy-2-oxoethyl)oxan-4-yl] 4-nitrobenzoate
  参考文献：
  名称：

  Versatile 8-Oxabicyclo[3.2.1]oct-6-en-3-one:  Stereoselective Methodology for Generating C-Glycosides, δ-Valerolactones, and Polyacetate Segments

  摘要：

  [GRAPHICS]A new rearrangement of functionalized methoxy glycosides and a regioselective as well as stereoselective intramolecular Michael addition giving delta -valerolactones and C-glycosides are described. Applications to the synthesis of marine natural products are reported, Chemoselective deprotection of benzylated hydroxy groups is assumed to be facilitated by 6-endo-tet interaction with the 1,3-dithiane functionality.

  DOI：

  10.1021/ol006737a
• 作为产物：
  描述：

  <(2R,4R)-6-methoxy-4-(4-methoxybenzyl)-oxy-tetrahydropyran-2-yl>-acetic acid methyl ester 在 三氟化硼乙醚 、 sodium hydride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 乙腈 为溶剂， 反应 25.0h， 生成 methyl 2-[(2S,4S,6R)-6-(1,3-dithian-2-ylmethyl)-4-hydroxyoxan-2-yl]acetate
  参考文献：
  名称：

  Versatile 8-Oxabicyclo[3.2.1]oct-6-en-3-one:  Stereoselective Methodology for Generating C-Glycosides, δ-Valerolactones, and Polyacetate Segments

  摘要：

  [GRAPHICS]A new rearrangement of functionalized methoxy glycosides and a regioselective as well as stereoselective intramolecular Michael addition giving delta -valerolactones and C-glycosides are described. Applications to the synthesis of marine natural products are reported, Chemoselective deprotection of benzylated hydroxy groups is assumed to be facilitated by 6-endo-tet interaction with the 1,3-dithiane functionality.

  DOI：

  10.1021/ol006737a

文献信息

• Versatile 8-Oxabicyclo[3.2.1]oct-6-en-3-one:  Stereoselective Methodology for Generating <i>C</i>-Glycosides, δ-Valerolactones, and Polyacetate Segments
  作者：A. Vakalopoulos、H. M. R. Hoffmann

  DOI：10.1021/ol006737a

  日期：2001.1.1

  [GRAPHICS]A new rearrangement of functionalized methoxy glycosides and a regioselective as well as stereoselective intramolecular Michael addition giving delta -valerolactones and C-glycosides are described. Applications to the synthesis of marine natural products are reported, Chemoselective deprotection of benzylated hydroxy groups is assumed to be facilitated by 6-endo-tet interaction with the 1,3-dithiane functionality.